Ethoxyquin → 2,2,4-Trimethyl-1,2-dihydro-6-quinolinol

HRID 25795

反応式

HRID 25795 の反応式
C([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([CH3:15])([CH3:14])[CH:8]=[C:7]2[CH3:16])C.B(Br)(Br)Br>ClCCl>[CH3:14][C:9]1([CH3:15])[CH:8]=[C:7]([CH3:16])[C:6]2[C:11](=[CH:12][CH:13]=[C:4]([OH:3])[CH:5]=2)[NH:10]1

参加物

4

反応物 2

HCID 3293EthoxyquinHCID 25134Boron tribromide2 回

生成物 1

HCID 5997992,2,4-Trimethyl-1,2-dihydro-6-quinolinol収率 45.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 31 g of 6-ethoxy-2,2,4-trimethyl-1,2-dihydroquinoline in 300 mL of dichloromethane was treated with 30 mL of boron tribromide dropwise at −78° C. After the addition of boron tribromide, the cooling bath was removed and the reaction mixture was allowed to warm to room temperature. The resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was then poured into crushed ice and the pH was adjusted to 9 with sodium bicarbonate. The product was the extracted into EtOAc. The organic solution was washed with water and brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by filtering through a short plug of silica gel eluting with 25% EtOAc in hexanes solution to give 12.4 g of 2,2,4-trimethyl-1,2-dihydroquinolin-6-ol as a light brown solid.

後処理

  1. customthe cooling bath was removed
  2. additionThe reaction mixture was then poured
  3. custominto crushed ice
  4. extractionextracted into EtOAc
  5. washThe organic solution was washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified
  10. filtrationby filtering through a short plug of silica gel eluting with 25% EtOAc in hexanes solution

出典と根拠

ORDレコード
ord-b788bc3ae1e342adb325965bd12b86b8
出典データセット
uspto-grants-2005_02
特許番号
US06858627B2

関連ノート

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